Synthesis of optically active, unnatural α-substituted glutamic acid derivatives by a chiral calcium-catalyzed 1,4-addition reaction

Tetrahedron Asymmetry

Volumn 21, Issue 9-10, 2010, Pages 1221-1225

  Tsubogo, Tetsu ^a   Kano, Yuichiro ^a   Ikemoto, Koki ^a   Yamashita, Yasuhiro ^a   Kobayashi, Sh ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; ACRYLIC ESTER; AZLACTONE DERIVATIVE; CALCIUM; ESTER DERIVATIVE; GLUTAMIC ACID; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHIRALITY; HYDROLYSIS; PRIORITY JOURNAL; SUBSTITUTION REACTION; SYNTHESIS;

EID: 77956709303     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.03.004     Document Type: Article

References (66)

1. M.C. Kemp, D.E. Jane, H.-W. Tse, and P.J. Roberts Eur. J. Pharmacol. 309 1996 79
2. R.J. Vandenberg, A.D. Mitrovic, M. Chebib, V.J. Balcar, and G.A.R. Jonston Mol. Pharmacol. 51 1997 809
3. N. Jullian, I. Brabet, J.-P. Pin, and F.C. Acher J. Med. Chem. 42 1999 1546
4. Synthesis of α,α-disubstituted quaternary amino acid derivatives: K. Maruoka, and T. Ooi Chem. Rev. 103 2003 3013
5. M.J. ODonnell Acc. Chem. Res. 37 2004 506
6. Y. Ohfune, and T. Shinada Eur. J. Org. Chem. 2005 5127
7. C. Nájera, and J.M. Sansano Chem. Rev. 107 2007 4584
8. T. Hashimoto, and K. Maruoka Chem. Rev. 107 2007 5656
9. H. Vogt, and S. Bräse Org. Biomol. Chem. 5 2007 406
10. M.I. Calaza, and C. Cativiela Eur. J. Org. Chem. 2008 3427
11. Selected examples of catalytic asymmetric reactions using azlactones. Dynamic kinetic resolution: D. Seebach, G. Jaeschke, K. Gottwald, K. Matsuda, R. Formisano, and D.A. Chaplin Tetrahedron 53 1997 7539
12. J. Liang, J.C. Ruble, and G.C. Fu J. Org. Chem. 63 1998 3154
13. A. Berkessel, F. Cleemann, S. Mukherjee, T.N. Müller, and J. Lex Angew. Chem., Int. Ed. 44 2005 807
14. Carboxy group transfer: J.C. Ruble, and G.C. Fu J. Am. Chem. Soc. 120 1998 11532
15. S.A. Shaw, P. Aleman, and E. Vedejs J. Am. Chem. Soc. 125 2003 13368
16. H.V. Nguyen, D.C.D. Butler, and C.J. Richards Org. Lett. 8 2006 769
17. C. Joannesse, C.P. Johnston, C. Concellón, C. Simal, D. Philp, and A.D. Smith Angew. Chem., Int. Ed. 48 2009 8914
18. 1,4-Addition reaction: J. Alemán, A. Milelli, S. Cabrera, E. Reyes, and K.A. Jørgensen Chem. Eur. J. 14 2008 10958
19. D. Uraguchi, Y. Ueki, and T. Ooi Science 326 2009 120
20. Other reactions: B.M. Trost, and X. Ariza Angew. Chem., Int. Ed. 36 1997 2635
21. B.M. Trost, C. Jäkel, and B. Plietker J. Am. Chem. Soc. 125 2003 4438
22. A.D. Melhado, M. Luparia, and F.D. Toste J. Am. Chem. Soc. 129 2007 12638
23. S. Cabrera, E. Reyes, J. Alemán, A. Milelli, S. Kobbelgaard, and K.A. Jørgen J. Am. Chem. Soc. 130 2008 12031
24. Y. Hayashi, K. Obi, Y. Ohta, D. Okamura, and H. Ishikawa Chem. Asian J. 4 2009 246
25. D. Uraguchi, Y. Ueki, and T. Ooi J. Am. Chem. Soc. 130 2008 14088
26. M. Terada, H. Tanaka, and K. Sorimachi J. Am. Chem. Soc. 131 2009 3430
27. J. Jiang, J. Qing, and L.-Z. Gong Chem. Eur. J. 15 2009 7031
28. D. Uraguchi, Y. Asai, and T. Ooi Angew. Chem., Int. Ed. 48 2009 733
29. Examples of 2-methyl glutamic acid derivatives. Catalytic asymmetric reaction: T. Kano, T. Kumano, and K. Maruoka Org. Lett. 11 2009 2023
30. Diastereoselective reaction: R. Chinchilla, L.R. Falvello, N. Galindo, and C. Nájera Angew. Chem., Int. Ed. 36 1997 995
31. Synthesis of glutamic acid derivatives using our catalysts: S. Saito, T. Tsubogo, and S. Kobayashi J. Am. Chem. Soc. 129 2007 5364
32. S. Kobayashi, T. Tsubogo, S. Saito, and Y. Yamashita Org. Lett. 10 2008 807
33. T. Tsubogo, S. Saito, K. Seki, Y. Yamashita, and S. Kobayashi J. Am. Chem. Soc. 130 2008 13321
34. Examples of catalytic asymmetric reaction using alkaline earth metal catalysts. Ba: Y.M.A. Yamada, and M. Shibasaki Tetrahedron Lett. 39 1998 5561
35. S. Saito, and S. Kobayashi J. Am. Chem. Soc. 128 2006 8704
36. A. Yamaguchi, N. Aoyama, S. Matsunaga, and M. Shibasaki Org. Lett. 9 2007 3387
37. K. Yamatsugu, L. Yin, S. Kamijo, Y. Kimura, M. Kanai, and M. Shibasaki Angew. Chem., Int. Ed. 48 2009 1070
38. A. Yamaguchi, S. Matsunaga, and M. Shibasaki J. Am. Chem. Soc. 131 2009 10842
39. Sr: M. Agostinho, and S. Kobayashi J. Am. Chem. Soc. 130 2008 2430
40. S. Kobayashi, M. Yamaguchi, M. Agostinho, and U. Schneider Chem. Lett. 38 2009 296
41. H.V. Nguyen, R. Matsubara, and S. Kobayashi Angew. Chem., Int. Ed. 48 2009 5927
42. R. Matsubara, B. Florian, H.V. Nguyen, and S. Kobayashi Bull. Chem. Soc. Jpn. 82 2009 1083
43. Ca: Y.M.A. Yamada, and S. Ikegami Tetrahedron Lett. 41 2000 2165
44. T. Suzuki, N. Yamagiwa, Y. Matsuo, S. Sakamoto, K. Yamaguchi, M. Shibasaki, and R. Noyori Tetrahedron Lett. 42 2001 4669
45. G. Kumaraswamy, M.N.V. Sastry, and N. Jena Tetrahedron Lett. 42 2001 8515
46. G. Kumaraswamy, M.N.V. Sastry, N. Jena, K.R. Kumar, and M. Vairamani Tetrahedron: Asymmetry 14 2003 3797
47. G. Kumaraswamy, N. Jena, M.N.V. Sastry, M. Padmaja, and B. Markondaiah Adv. Synth. Catal. 347 2005 867
48. G. Kumaraswamy, N. Jena, M.N.V. Sastry, and G. Ramakrishna ARKIVOC 2005 53
49. Coordinative chiral calcium catalyzed reactions: T. Tsubogo, Y. Yamashita, and S. Kobayashi Angew. Chem., Int. Ed. 48 2009 9117
50. T. Poisson, T. Tsubogo, Y. Yamashita, and S. Kobayashi J. Org. Chem. 75 2010 963
51. For the synthesis of pybox: G. Desimoni, G. Faita, and P. Quadrelli Chem. Rev. 103 2003 3119
52. H.A. McManus, and P.J. Guiry Chem. Rev. 104 2004 4151
53. H. Nishiyama, M. Kondo, T. Nakamura, and K. Itoh Organometallics 10 1991 500
54. A.D. Gupta, D. Bhuniya, and V.K. Singh Tetrahedron 50 1994 13725
55. G. Desimoni, G. Faita, M. Guala, and C. Pratelli Tetrahedron: Asymmetry 13 2002 1651
56. M.K. Tse, S. Bhor, M. Klawonn, G. Anilkumar, H. Jiao, C. Döbler, A. Spannenberg, W. Mägerlein, H. Hugl, and M. Beller Chem. Eur. J. 12 2006 1855
57. Transformation of azlactones: C. Nájera, T. Abellán, and J.M. Sansano Eur. J. Org. Chem. 2000 2809
58. T. Yamada, T. Okada, K. Sakaguchi, Y. Ohfune, H. Ueki, and V.A. Soloshonok Org. Lett. 8 2006 5625
59. Reported examples: D. Obrecht, U. Bohdal, J. Daly, C. Lehmann, P. Schönholzer, and K. Müller Tetrahedron 51 1995 10883
60. R. Chinchilla, N. Galindo, and C. Nájera Synthesis 1999 704
61. G. Tang, H. Tian, and D. Ma Tetrahedron 60 2004 10547
62. Amino alcohols synthesis: S.E. Denmark, R.A. Stavenger, A.-M. Faucher, and J.P. Edwards J. Org. Chem. 62 1997 3375
63. P. Müller, and C. Boléa Helv. Chim. Acta 84 2001 1093
64. N.W. Alcock, G. Clarkson, P.B. Glover, G.A. Lawrance, P. Moore, and M. Napitupulu Dalton Trans. 2005 518
65. 2,6-Pyridinedicarboxamide is commercially available.
66. C.-W. Kuo, J.-L. Zhu, J.-D. Wu, C.-M. Chu, C.-F. Yao, and K.-S. Shia Chem. Commun. 2007 301